Hydrochloric Acid → HCID 58074319, compound

Temperature

-78 °C

HNiPr2 (246 μL, 1.74 mmol, 3.0 Eq) was dissolved in anhydrous THF (10 mL) and cooled to −78 ° C. under nitrogen. 2.5 M BuLi in hexanes (700 μL, 1.74 mmol, 3.0 Eq) was added dropwise and the reaction stirred at −78 ° C. for 15 minutes then warmed to 0° C. for 30 minutes. The reaction was cooled to −78 ° C. and 1-[1-(2-chloro-phenyl)-ethyl]-1,2,3,4-tetrahydro-thieno[3,2-e][1,4]diazepin-5-one (178 mg, 0.58 mmol, 1.0 Eq) was in anhydrous THF (5 mL) was added dropwise. The reaction was stirred at −78 ° C. for 2 hours. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane (355 μL, 1.74 mmol, 3.0 Eq) in anhydrous THF (5 mL) was added and the reaction stirred at −78 ° C. for 20 minutes them warmed to ambient temperature for 1.5 hours. 1M HCl (20 mL) was added and the mixture extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine (40 mL), dried (MgSO4) and concentrated in vacuo. The yellow oil obtained was used without further purification; 1H NMR (DMSO D6) 1.28 (12H, s), 1.51 (3H, d), 2.93-2.99 (1H, m), 3.03-3.13 (2H, m), 3.20-3.26 (1H, m), 5.32 (1H, dd), 6.19 (1H, br s), 7.20-7.28 (3H, m), 7.33-7.36 (2H, m); LC/MS M+1 (obs.) 433.4.

1. temperaturethen warmed to 0° C. for 30 minutes
2. temperatureThe reaction was cooled to −78 ° C.
3. additionwas added dropwise
4. stirringThe reaction was stirred at −78 ° C. for 2 hours
5. stirringthe reaction stirred at −78 ° C. for 20 minutes them
6. temperaturewarmed to ambient temperature for 1.5 hours
7. extractionthe mixture extracted with EtOAc (3×40 mL)
8. washThe combined organic extracts were washed with brine (40 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo
11. customThe yellow oil obtained
12. customwas used without further purification

ORD record

ord-c76cab4f7e37438db54d624375891b7d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399458B2